Four years ago, Barry Blitt drew a series of “spots”—the small, captionless illustrations that appear throughout each week’s magazine—that showed Donald Trump as, among other things, Superman, the Cheshire cat, and a piece of toast flying out of a toaster. When we asked him then whether he hoped that Trump would enter the Presidential race, he had said yes, but added, “Having just drawn him fifteen times in the space of a day for...